Process for preparing C1 -C5 alkyl 5-(substituted-phenoxy)-2-nitrobenzoate

ABSTRACT

A process of preparing C 1  -C 5  alkyl 5-(substituted-phenoxy)-2-nitrobenzoate such as a process for preparing methyl 5-(2&#39;,4&#39;-dichlorophenoxy)-2-nitrobenzoate by the coupling reaction of methyl 2-nitro-5-chlorobenzoate with the potassium salt of 2,4-dichlorophenol in dimethylformamide solvent to produce a reaction product mixture containing desired ester product and byproduct potassium 5-(2&#39;,4&#39;-dichlorophenoxy)-2-nitrobenzoate. The yield of desired ester product is increased by a process that comprises reacting said reaction product mixture in situ, with methyl chloride at a pressure of about 440 mm. Hg. to about 50 psig., for between about 0.5 hour and about 4 hours, and at a temperature between about 75° C. and about 105° C. In a specific embodiment the process is carried out on bench scale at a temperature of between about 75° C. and about 100° C. and at a pressure of between about 10 psig. and about 50 psig. In another specific embodiment the process is carried out on plant scale at a temperature of between about 75° C. and about 105° C. and at a pressure of between about 440 mm. Hg. and about 760 mm. Hg.



